Amine-Catalyzed Decarboxylative Aldol Reaction of β-Ketocarboxylic Acids with Trifluoropyruvates
Decarboxylative aldol reaction of aliphatic carboxylic acids is a useful method for C−C bond formation because carboxylic acids are an easily available class of compounds. In this study, we found that the decarboxylative aldol reaction of tertiary β-ketocarboxylic acids and triflu...
| Main Authors: | , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2019-07-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/24/15/2773 |
| _version_ | 1811267751123091456 |
|---|---|
| author | Ryouta Kawanishi Shinya Hattori Seiji Iwasa Kazutaka Shibatomi |
| author_facet | Ryouta Kawanishi Shinya Hattori Seiji Iwasa Kazutaka Shibatomi |
| author_sort | Ryouta Kawanishi |
| collection | DOAJ |
| description | Decarboxylative aldol reaction of aliphatic carboxylic acids is a useful method for C−C bond formation because carboxylic acids are an easily available class of compounds. In this study, we found that the decarboxylative aldol reaction of tertiary β-ketocarboxylic acids and trifluoropyruvates proceeded smoothly to yield the corresponding aldol products in high yields and with high diastereoselectivity in the presence of a tertiary amine catalyst. In this reaction, we efficiently constructed a quaternary carbon center and an adjacent trifluoromethylated carbon center. This protocol was also extended to an enantioselective reaction with a chiral amine catalyst, and the desired product was obtained with up to 73% enantioselectivity. |
| first_indexed | 2024-04-12T21:09:41Z |
| format | Article |
| id | doaj.art-91fb2d134f62435782df8b4b629b65e7 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-04-12T21:09:41Z |
| publishDate | 2019-07-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-91fb2d134f62435782df8b4b629b65e72022-12-22T03:16:38ZengMDPI AGMolecules1420-30492019-07-012415277310.3390/molecules24152773molecules24152773Amine-Catalyzed Decarboxylative Aldol Reaction of β-Ketocarboxylic Acids with TrifluoropyruvatesRyouta Kawanishi0Shinya Hattori1Seiji Iwasa2Kazutaka Shibatomi3Department of Applied Chemistry and Life Science, Toyohashi University of Technology, 1-1 Hibarigaoka, Tempaku-cho, Toyohashi 441-8580, JapanDepartment of Applied Chemistry and Life Science, Toyohashi University of Technology, 1-1 Hibarigaoka, Tempaku-cho, Toyohashi 441-8580, JapanDepartment of Applied Chemistry and Life Science, Toyohashi University of Technology, 1-1 Hibarigaoka, Tempaku-cho, Toyohashi 441-8580, JapanDepartment of Applied Chemistry and Life Science, Toyohashi University of Technology, 1-1 Hibarigaoka, Tempaku-cho, Toyohashi 441-8580, JapanDecarboxylative aldol reaction of aliphatic carboxylic acids is a useful method for C−C bond formation because carboxylic acids are an easily available class of compounds. In this study, we found that the decarboxylative aldol reaction of tertiary β-ketocarboxylic acids and trifluoropyruvates proceeded smoothly to yield the corresponding aldol products in high yields and with high diastereoselectivity in the presence of a tertiary amine catalyst. In this reaction, we efficiently constructed a quaternary carbon center and an adjacent trifluoromethylated carbon center. This protocol was also extended to an enantioselective reaction with a chiral amine catalyst, and the desired product was obtained with up to 73% enantioselectivity.https://www.mdpi.com/1420-3049/24/15/2773decarboxylationaldol reactiontrifluoromethyl compoundscinchona alkaloidsenantioselective synthesischiral amine catalyst |
| spellingShingle | Ryouta Kawanishi Shinya Hattori Seiji Iwasa Kazutaka Shibatomi Amine-Catalyzed Decarboxylative Aldol Reaction of β-Ketocarboxylic Acids with Trifluoropyruvates Molecules decarboxylation aldol reaction trifluoromethyl compounds cinchona alkaloids enantioselective synthesis chiral amine catalyst |
| title | Amine-Catalyzed Decarboxylative Aldol Reaction of β-Ketocarboxylic Acids with Trifluoropyruvates |
| title_full | Amine-Catalyzed Decarboxylative Aldol Reaction of β-Ketocarboxylic Acids with Trifluoropyruvates |
| title_fullStr | Amine-Catalyzed Decarboxylative Aldol Reaction of β-Ketocarboxylic Acids with Trifluoropyruvates |
| title_full_unstemmed | Amine-Catalyzed Decarboxylative Aldol Reaction of β-Ketocarboxylic Acids with Trifluoropyruvates |
| title_short | Amine-Catalyzed Decarboxylative Aldol Reaction of β-Ketocarboxylic Acids with Trifluoropyruvates |
| title_sort | amine catalyzed decarboxylative aldol reaction of β ketocarboxylic acids with trifluoropyruvates |
| topic | decarboxylation aldol reaction trifluoromethyl compounds cinchona alkaloids enantioselective synthesis chiral amine catalyst |
| url | https://www.mdpi.com/1420-3049/24/15/2773 |
| work_keys_str_mv | AT ryoutakawanishi aminecatalyzeddecarboxylativealdolreactionofbketocarboxylicacidswithtrifluoropyruvates AT shinyahattori aminecatalyzeddecarboxylativealdolreactionofbketocarboxylicacidswithtrifluoropyruvates AT seijiiwasa aminecatalyzeddecarboxylativealdolreactionofbketocarboxylicacidswithtrifluoropyruvates AT kazutakashibatomi aminecatalyzeddecarboxylativealdolreactionofbketocarboxylicacidswithtrifluoropyruvates |